489-84-9 Usage
Chemical Properties
DARK BLUE LOW MELTING CRYSTALLINE SOLID
Originator
AZ 8,Millet Roux
Uses
Different sources of media describe the Uses of 489-84-9 differently. You can refer to the following data:
1. antioxidant, inhibits lipid peroxidation inhibitor, antiinflammatory, hepatoprotectant; LD50(rat) 1550 mg/kg po
2. Guaiazulene can be used as a starting material for the synthesis of:Azulene-based dye molecules such as 3-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanoacrylic acid and 5-(7-isopropyl-1,4-dimethylazulen-3-yl)-2-cyanopenta-2,4-dienoic acid.Stilbazulenyl nitrone, a second-generation azulenyl nitrone which can be used as a chain-breaking antioxidant.Bis-azulenyl based near-infrared fluorescence quencher.
Manufacturing Process
10 kg a gum of Guacum officinale was heated with 3-4 kg of sulfur to 130°C.
The heating was slowly continued for 220°C under the nitrogen. The formed
water steam was removed with the nitrogen current. The temperature should
be higher 100°C in order to the water didnt fall into reaction mixture. H2S was
obtained simultaneously the dehydrogenation and removed with water steam.
Hydrogen sulfide was connected in an alkaline trap.
When a H2S discharge stopped, the temperature was decreased to 120°C and
the reaction mixture was distilled in vacuum 1-20 mm. The distillate had deep
blue color and contained 6-7 kg oil with 20% of 7-isopropyl-1,4-
dimethylazulene. It was dissolved in the 5-10 volumes of light petroleum,
shook with sodium hydroxide for removing the sulfur containing substaneces,
washed to neutral. Then petrolem layer was mixed with 10-15 L 62% H2SO4
for removing the by-products, the petroleum layer lost the blue color and the
desired substance was in sulphuric acid layer. The last one was shook with ice
and NaOH. As a result about 7% NaSO4 solution in sulfuric acid was obtained.
It was diluted and azulene gave an emulsion, which was extracted with 10 L
of petrolem and distilled. The 7-isopropyl-1,4-dimethylazulene is distilled at
167°-168°C/12 mm. Yield 10-15%.
Therapeutic Function
Antiinflammatory
General Description
This substance is a primary reference substance with assigned absolute purity (considering chromatographic purity, water, residual solvents, inorganic impurities). The exact value can be found on the certificate. Produced by PhytoLab GmbH & Co. KG
Purification Methods
It forms blue-violet plates from EtOH. Also redistil it in vacuo until distillate solidifies. UV has max at 284nm (log 4.6, heptane). The picrate has m 122o(EtOH). [Beilstein 5 III 1677, 5 IV 1751.]
Check Digit Verification of cas no
The CAS Registry Mumber 489-84-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,8 and 9 respectively; the second part has 2 digits, 8 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 489-84:
(5*4)+(4*8)+(3*9)+(2*8)+(1*4)=99
99 % 10 = 9
So 489-84-9 is a valid CAS Registry Number.
InChI:InChI=1/C15H18/c1-10(2)13-7-5-11(3)14-8-6-12(4)15(14)9-13/h5-10H,1-4H3
489-84-9Relevant articles and documents
ALISMOL AND ALISMOXIDE, SESQUITERPENOIDS OF ALISMA RHIZOMES
Oshima, Yoshiteru,Iwakawa, Tsuneo,Hikino, Hiroshi
, p. 183 - 186 (1983)
From the crude drug 'takusha', wich is the rhizomes of Alisma plantago-aquatica var. orientale, two new sesquiterpenoids, alismol and alismoxide, have been isolated.Their structures have been estabished on the basis of chemical and physical evidence to be 1β,5β-guaia-6,10(15)-dien-4-ol and 4,10-epoxy-1β,5β-guaia-6-ene, respectively. - Key Word Index: Alisma plantago-aquatica var. orientale; Alismataceae; sesquiterpenoid; guaiane skeleton; alismol; 1β,5β-guaia-6,10(15)-dien-4-ol; alismoxide; 4,10-epoxy-1β,5β-guaia-6-ene
Evstratova et al.
, (1967)
Plattner,Fuerst,Marti
, p. 2452,2460 (1949)
-
Ukita et al.
, p. 4584,4586 (1954)
-
Hoffmann,Siegel
, p. 533,535 (1975)
Rudloff,Nair
, p. 421,424 (1964)
Naves,Papazian,Perrottet
, p. 302,324 (1940)
Approach to the blues: A highly flexible route to the azulenes
Carret, Sebastien,Blanc, Aurelien,Coquerel, Yoann,Berthod, Mikael,Greene, Andrew E.,Depres, Jean-Pierre
, p. 5130 - 5133 (2007/10/03)
(Chemical Equation Presented) A palette of blues: Chlorobicyclo-[5.3.0] decatrienones are readily prepared from cycloheptatrienes by cycloaddition of dichloroketene, ring expansion with a diazoalkane, and dehydrochlorination in dimethylformamide. These compounds are used as intermediates in the regiocontrolled synthesis of a wide variety of natural and nonnatural azulenes (see scheme).
Reaction of Guaiazulene with Bromine in Hexane and in Aqueous Tetrahydrofuran
Nozoe, Tetsuo,Shindo, Kimio,Wakabayashi, Hidetsugu,Kurihara, Teruo,Uzawa, Jun
, p. 687 - 688 (2007/10/02)
2-Bromoguaiazulenium bromide and 3,3-dibromo guaiazulenium bromide were obtained respectively from the reaction of guaiazulene and its 3-bromo compound with 1 equivalent of bromine in hexane at -20 deg C.The former compound afforded in methanol a mixture of guaiazulene, 3,3'-biguaiazulene, and oligomers, and gave 3-bromoguiazulene quantitatively with alkali.Dibromoguiazulenium bromide afforded with further moles of bromine in aqueous THF a mixture of guaiazulenequinone, 3-bromo-1-hydroxyquaiazulen-5-one, and a dark blue solid A in different ratios depending on the reaction conditions.